I live in the United States. The DMCA and similar laws apply to me, and even innocent and morally permissible software development practices can be illegal. Specifically, anything that involves disabling or interfering with DRM is prohibited.

While criminal charges are unlikely (but not unheard of), civil litigation is certainly possible and is often somewhat misaimed. Various legal theories advanced by lawyers who push this litigation include concepts like "contributory infringement" make it so that even forums where such things are discussed can be attacked.

Is it permissible here to discuss "cracking" software, disabling DRM, or similar activities? Are there guidelines for how much and what should be said? Should specific software titles or product models/brands be left out? Are these questions only allowed if the questioner is doing it for personal use, do you discourage someone who will release their project to the public?

2 Answers
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It is quite common to have questions asking about ways to bypass all sorts of protection mechanisms here. I do not think DRM should be any different.

It is impossible for us to know wether what you're doing is legal or not in your country unless you admit you're breaking a law (in which case the community will avoid providing any help).

Moreover, we can't identify a question about DRM without OP mentioning it, it could just as well be any other protection software not protected by DRM.

What's illegal in one country can be perfectly legal in another. Such examples are Germany's explicit loosen laws regarding Clean Room methodologies, it's impossible to have one rule of thumb here.

Any legal issues between the stack exchange forums and third parties should be addressed and handled by Stack Exchange. We honestly cannot make that decision for them, but only offer our opinion.

I think the best we can do as a community is refuse helping and warn anyone clearly breaking laws he's subject to and where someone should tread carefuly, but we cannot and shouldn't enforce any country specific laws (especially when we're dealing with flexible interpertations of the law).

On the other hand, we should make sure Stack Exachnge is aware of the complexities of legal issues when it comes to reverse engineering and make sure they're not in violation of any law.

Your questions have to be phrased like a politician to be careful not to implicate yourself in some crime that may or may not even have occurred, or that someone may or may not care about. This varies from country to country.